What Would and Should Have Been
by Fallen Lights
Summary: What would have really happened if Dean got through to Sam in time, what struggles would the brothers then face in the world with Lilith still living. Sorry no Slash, for all you fans xP
1. The Beginning of the End

**I am soooo sorry for the quotation mess up before my computer was all messed up!!!**

**Well, this is my first try at a Supernatural fanfic... I hope you all like it, I will take any comments or criticism!! It is right when Sam ran away to kill Lilith and Dean was locked away by Zechariah.**

**Disclaimer: I do not own Supernatural or any of it s characters**

Feelings, they were a strange thing. For the first time in his life Castiel was confused. It was a strange feeling not knowing what to do. It seemed like everything had changed since he met the Winchester brothers. They questioned him, and his beliefs. They even made him question himself. This bothered him more then it should, he was close to disobeying and he knew it.

"Excuse me?" A small voice brought him back to the present. A small girl was standing beside him innocent and insignificant. If only she knew the world was coming to an end. Have you seen my puppy, he ran away yesterday. She handed him a poster of a small dog. Still Castiel stayed silent. If you see him please return him, I miss him a lot. She gave him a meaningful smile before turning around to go to the next person. He didn't understand it, how humans could become so attached to things as unresponsive as a dog. The girl was so sure, so sure of her life and who or what she loved. For that alone Castiel envied her.

* * *

The room was large, it was fancy. It was too fancy for Dean s liking. He scanned the room, looking for a way out. Even though he had been doing that for the past hour he still hoped. Sam would already be on his way to kill Lilith and there was nothing he could do stuck in here. Still he had one hope, Castiel. He had asked Zechariah to see him almost a half hour ago, and now dean was getting pissed. He walked over to a table by the far wall. There was a statue of an angle. Thinking of nothing better to do he flicked it off the table with his finger.

* * *

Castieal didn't know what to do. Dean wanted to see him. He couldn't take making him stay there any more. Nit if he had to meet him again. Still he had to go, or the others might realize his doubts. When he entered the room Dean had tipped over a statue. "You asked to see me." No matter how much he wished he didn't.

"Yeah," he paused. "I need to talk to you." He shifted his weight from one foot to the other. He didn't meet the angels eyes.

"Well then speak." It was getting harder every word.

"I need you to take me to my brother. You know what s going on and you know that it is wrong." Finally Dean lifted his gaze to meet Castiel's. "You are my last hope to stop this, to make sure that the apocalypse doesn't happen." A tense silence followed his words. He didn't have anyone else to turn too, still the angel didn't even blink.

Castiel had feared this moment for a long time. Which was strange, he had never known fear or what it felt like before in his life. Now was the time for him to really choose his side in this war. For him to decide what to believe. It occurred to him that he already knew the answer, deep down in his heart. This astounded Castiel for he thought he knew himself well. Not even bothering to explain himself he rolled up his sleeve and pulled out his knife. He made a clean slit just before his elbow. The blood instantly began to drip to the floor. He dipped the fingers of his other hand in the blood and bean to draw a sign on the wall. Right before he finished Zechariah showed up.

"What do you think you are doing?" He was enraged and began moving forward.

"The right thing," Castiel slammed his palm into the middle of the sign. In a bright light Zechariah vanished from sight. Relief swelled through his body so much that it was almost overwhelming.

"What the hell did you do?" Dean still hadn't looked away from the spot where Zechariah stood moments before.

"Banished him for now, but he will be back. I don t know where Sam is but I know someone who does." He waited for a reply out of courtesy.

"Well then what the hell are we waiting for!" With that Castiel lifted two fingers to Dean s forehead and everything went black.

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**Well that is it, tell me what you think!! I hope to get some reviews to see if the story is worth continuing...**

**Please Review!!**


	2. The Death That Shall Never Happen

**Well, this is my second chapter and I hoped you all liked the first!**

**I'm not to sure where I will end up with this but I just write as it comes to me...**

**Thank you to ****Maggiedoodle18**** for reviewing on chapter 1**

**Disclaimer: I do not own Supernatural**

* * *

Not to long ago Chuck lived a pretty average life. He was just making it by as a writer of what he thought to be a fictional series. Well that is what he thought. Turns out Sam and Dean Winchester were real people and he was a protected profit of the lord. Well isn't he lucky... Still on a dull grey afternoon the last thing he expected was Dean. Well when had he ever got what he expected. One second he was alone and then the next Dean was there with Castiel.

"Chuck we need your help." Dean sounded like he was in a hurry, the last time that happened he ended up in a hotel room with a demon. "I need you to tell me where sam is." Well that was easy enough being a profit he knew exactly where Sam was.

"Hold on I will look it up." He raced to his computer and picked up the first paper on a stack. Scanning the page he looked for an address, he almost had it when the room began to shake. Panicked he looked up to the other two.

"It must be the archangel, you must hurry." Castiel watched the ceiling as he spoke, Chuck went back to quickly scanning.

"He's at St. Mary's it's a convent." Chuck looked at the two waiting for there next move.

"You must stop Sam I will hold them all off." Castiel lifted his two fingers back to Dean's head once more and everything for him went back to black.

* * *

When his vision finally came back and the world stopped spinning Dean was in awe. The convent was old, very old. He was at the end of a long corridor. Bodies lined the hallway, at the end was a large wooden door. He broke into a run and slammed into the wood, it didn't budge. "Sam!" He tried banging on the door, but still nothing happened. He could hear voices on the other side and knew he was almost to late. He hit it again and it began to move. _I need to stop him, I need to save him! _That single thought raced through his head as he pushed the door forward. When the crack was big enough he flung himself in the room. "Sam stop!" He could see his brother now, holding Lilith with his mind. What he didn't see was Ruby. She came out of no where and knocked him to the ground. His head hit concrete and everything went fuzzy.

"No Dean!" Sam had finally noticed his brother in the room. Ruby had knocked him to the ground, he released his hold on Lilith and focused it all on Ruby. She wasn't as strong, but this was personal. He had trusted her, and for some reason she was attacking Dean. No matter what she was still a demon and he needed to pick Dean over her, but he couldn't kill her. "Go back to hell you bitch." Focusing his mind he pulled her from the body and sent her back to the pit.

"Watch out Sam." Dean pointed to something over Sam's shoulder. As he turned Lilith took a swing. Her fist connected with his jaw and sent him reeling. He stood up and tried to pin her but nothing happened.

"Seems you used up too much of your juice on Ruby." She smiled and started to advance. Dean stood as well and held the demon knife up and ready. "I'll see you soon Sam." Lilith bent her head back and left the body. After the body fell there was silence in the room. Sam turned to Dean but didn't speak.

"Are you alright?" Blood was dripping down the side of Deans head that he hit. He had come to save Sam, even after he left without even telling Dean where he was going. He risked his life even when Sam wasn't listening.

"Look Dean I am so sorry for everything I-" He stopped as Dean raised his hand.

"It's alright, and I asked you if you were alright." He seemed to not want to go into the whole story now so Sam just nodded. "Alright then lets get out of here and somehow get back to the impala." He led the way out of the convent.

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**Well that's it for chapter two, I hope you enjoyed.**

**I will try to post a new chapter at least once a week!**

**Please review I want to hear what you think!!!!**


	3. The Most Hated Car

**Well here goes chapter three, I hope you all are enjoying!**

**Disclaimer: If I did own Supernatural I wouldn't be sitting here right now...**

* * *

"Where the hell are we?" Dean was getting anoyed. There was a single dirt road in front of them, but other then that, nothing.

"Ilchester, Maryland." Sam looked around, he knew they didn't have a choice but it was the last car he wanted to take. "Come on, we parked further up the road." A hard silence came over the two, by we Dean knew Sam ment him and Ruby. They started to walk down the road and around the corner, the only sound was the gravel crunching under their feet.

"Well that's a real incinpicuous car Sammy." Sam grimiced at Ruby's car. She had liked to drive something fast. Still it was a car and it meant they didn't have to walk.

"I'll drive." Sam pulled the keys out of his pocket and slipped into the drivers seat. Dean slowly got into the passangers seat, but looked uncomfertable sittting there. "Where did you leave the Impala?" He started the car as he spoke.

"Bobby's house." Dean looked out the side window as he spoke. "We need to go to Chuck's first, that's where I left Cas." There was an emotion in Dean's voice that Sam didn't understand. He thought for a second until it came to him. _Chuck is protected by an archangel, so what happened to Cas?_ Then it hit him like a wave, it would have killed Castiel. The archangel would have ripped him apart. Sam pushed his foot down a little harder on the gas.

* * *

Once again Chuck found himself wishing to be someone else. Anyone else would have been better then him. He wanted to blame Sam and Dean, to hate them for all of this. Of course he couldn't because he knew what they had been through. Once Dean left the archangel came. Castiel tried but he didn't stand a chance. The archangel ripped him appart. When everything was over Chuck went straight to the whiskey. Now that things were back to normal the visions came back too. He knew Sam didn't kill Lilith and he knew they were coming. So he went and sat on what was left of his couch and waited.

* * *

The car slowed to a stop outside Chuck's house. It was the longest most uncomfertable car ride Dean had ever been on, and he spent most of his life in a car. The car itself was nice, but too new and shinny. It also smelt like Ruby. That was the most disturbling thing.

"We're here." Sam hadn't spoken a word the whole ride. He got out of the car and looked back at it in distaste. "Maybe Chuck wants to trade cars." He led the way up the front step.

"We could only hope." Dean muttered under his breath, Chuck would know whos car it was. When they made it to the front door Dean pulled out his gun. The front door was open a crack. He looked at Sam and motioned that he would go first. Raising his gun he moved forward checking both left and right before moving into the other room. That is where Chuck was sitting.

"I wish I could say I am glad to see you." Chuck sounded dull and lifeless.

"What happened to Cas." Dean couldn't take anymore jokes or beating around the bush.

"It ripped him appart, there was nothing left when it was done." He took a swig fromt the whiskey bottle before offering it to Dean. He took the bottle from Chuck gratefully. The whiskey tasted warm and hot in his throat, but it washed some of his misery away.

"What happens next Chuck?" Sam looked right at him expecting all the answers.

"Honestly, I don't know. All I have seen is you guys heading back to Bobby's house." He sighed, wishing he had the answers.

"Well then we will be on our way, oh and do you want to trade-" Sam was cut off by Chuck.

"Hell no, I will never go near that car." He took another large swig of wiskey.

* * *

There was one good thing about the car. It was the only good thing about it Dean could think of. The car was fast. They were racing down the highway heading back to Bobby's house and making great time. That was until the sirens sounded behind them. "Ah, what the hell." He punched the dash while the car rolled to a stop. Waiting in the silence Sam started to look for his fake license. He rolled down the window when the officer approched. The officer drew his gun and pointed it in the car.

"Come out with your hands up where I can see them!" The Winchester boy's did as he asked and were sent to the hood.

"Hands on your head!" First the officer pulled Sam's hands down and handcuffed them, then he moved on to Dean.

"What the hell are we being arrested for!" Dean struggled against the officer, even though he was the one with the gun.

"This car has had a stolen car report on it for the past couple of months." Dean turned to glare at Sam who just shrugged.

"I think we should have just walked." Dean glared at the car that had given them so much hell.

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**Well thats it for chapter three!**

**I hope you all are enjoying it, and please review!**


	4. Jail House Blues

**Disclaimer: I don't own Supernatural**

**I hope you enjoy**

...

Jail. It was an annoying place. Once again the cops were baffled. Dean was sitting cuffed to a desk when the cops walked away with his fingerprints. Sam shifted beside him. "We are so screwed." He shook his head and ran his fingers through his hair.

"I know Sammy, we need to get out of her, before those results get back."

"Oh sure Dean, how are we going to do that?"

"Well I don't know." They lapsed into silence waiting for the authorities to return. It was twenty minutes later when they finally did.

"Alright you're coming with us for questioning, and you can stay here with my partner." The cop moved forward and unattached Sam from the table. Two officers took him out and the other sat down. He was short, well dressed with his dark hair slicked back. He opened a folder and read for a moment before looking back up at Dean.

"So you purchased the car from an online dealer?" His gaze was intense and he didn't waver.

"That's what we said, he told us that it was his and sold it to us." Lying was easy, convincing the cops after they saw his real record wouldn't be.

"So, Frank, if that is your name. What was the name of this guy who sold it to you?"

"James Wilder, he said he bought it new." Dean was sure that Sam would use the same name, that's just how things worked. As the officer wrote down the name someone entered and passed him a folder. His eyes widened and Dean cursed under his breath. Computers were getting way to fast.

"So, Dean Winchester. Apparently faked your death once before now, convicted of murder on about five or six accounts, bank robbery, attempted murder, credit card fraud, grave desecration, and now an act of terrorism." A look of pure disgust crossed his face, and Dean was confused.

"What act of terrorism?"

"Back in Colorado the building that exploded shortly after you were pronounced dead." He added air quotes around pronounced dead.

"I would like my phone call now." Bobby could get them out, and if he couldn't no one could.

"Alright I will have that arranged, by the way my name is agent Gregory." He stood and walked out, the door latching shut behind him.

"Oh we are so screwed."

...

They put Sam in a room on the other side of the building, his fingers drummed against the desk as he thought. They had left him for awhile now and he guessed they were interrogating Dean first. The man that stayed with Dean entered with a folder and slid it across the table to him. "It's an interesting read." Sam pulled it to him and opened it with a grimace. "I'm agent Gregory."

"Wish I could say it's nice to meet you." Sam grumbled as he read. The terrorism act was new but expected.

"So you're Sam Winchester, the younger brother. Your girlfriend Jessica died in a fire and that's when you reunited with Dean." Sam turned his head to the side, he had stopped drumming his fingers but his foot had started tapping. He knew why, but he pushed the thought to the back of his head.

"Well why do I need to confirm it if you have my finger prints as proof?" He was agitated and it was showing.

"So how did you do it?" He sat down and pulled the file back toward him. "How did you fake your death? I know your brother's done it once before."

"I want my phone call." They needed Bobby, and they needed him quick. Still there was something else Sam needed more, he was weakening and he knew it. One thought in the back of his mind never went away. It was pulsing like a heart beat getting faster, blood...

...

A normal life, that is what Bobby craved for. Ever since he met the Winchester's he knew that wasn't possible. They came to him when they had a problem they couldn't solve, and what they couldn't solve was normally bad. As he was reading up on a case he got the one phone call that would ruin his day. "Hello."

"Hey Bobby, it's dean. Uh we're kind of in jail." Bobby swore, though the news was better then he thought.

"What happened?"

"Ruby's car, we were driving it, it was stolen."

"Alright where are you?" Bobby got out a piece of paper and a pen.

"La Crosse, Wisconsin." Dean sounded worn out.

"Okay, I'll figure something out." He sighed and gripped the phone tighter.

"Hurry." The line went dead. Now it was up to him, to get two of the worlds greatest hero's out of jail.

"Well, I need more beer."

...

**I'm sorry that I've haven't updated in so long, and that it's so short**

**Thought it was better to get back into the swing of things**

**Please review**


	5. Handcuffed

**Disclaimer: I don't own Supernatural**

**Enjoy!**

...

Death. For humans it was simple, they could predict where they would end up depending on there life. For other creatures it was not. What happened to an Angel if it died? Would they live in heaven like humans, or just disappear. The thought crossed his head a lot, ever since he ran he became unsure. Gabriel was now known by many other names including Loki or The Trickster. He couldn't stand the way his family acted. Always hurting and betraying each other. So he left. Walking slowly down the sidewalk he was left to his thoughts.

"Excuse me mister." A little boy was behind him on a bike. He shifted to the side so he could pass. He had been keeping track of the Winchester's, they were important and every angle knew it. Right now he had followed them to Wisconsin after they had an run in with Lilith. When he did find them he decided to help them. His plan would go into motion in five minutes.

...

Derek was proud of his work. He had made it to the front desk at the local police office. Today he put together the files on two new fugitives they booked. The Winchester's were his biggest case he ever helped on. The day was going great until they showed up. "Alright everyone guns on the floor hand on your head! We have explosives surrounding the building and they'll blow it with me in here unless you give us what we want!" The man was tall and in a suit that resembled one of a swat member. As he walked further in there was two knocks on every window in the building.

"Alright sir calm down." The chief slowly stood and placed his gun on the ground, others followed.

"That sound was my colleagues knocking on every window in the building, now think how many windows you have." Derek thought about it; there were a lot.

"Now sir, don't do something you'll regret." The chief took a small step forward and the man too three to him, a gun in hand.

"I wont, just release the Winchester's and I'll let you live." He smiled and pointed the gun at the chief from two feet away.

"The Winchester's?"

"Yes, the two boys you booked today with the impressive track record. I need their advice so I'm taking them with me." He moved forward more and pulled the chiefs keys from his pocket. "So who's going to get them before I have this place blow! I'll start shooting in ten if no one moves!" He threw the keys on the ground and an officer shot forward grabbed the keys and ran toward the cells. He came back within a minute with the two handcuffed together.

"What the hell is going on here." The shorter of the two looked around in confusion.

"Well they look superb officers, I'll take them from here. Boys out the front please." He motioned with his gun and the Winchester's walked slowly in the direction.

"You will regret this sir." The chief added the threat as the man followed the two out. No one moved for a few moments after the door clicked shut. Derek turned to look at the chief.

"This is my two weeks notice."

...

Dean was baffled to say the least He followed the man that he deamed to be the greatest guy in the world out of the building to a black civic. He turned to them and began rapidly. "You take this car and you drive, don't stop until you're out of the state. Get a new car and take a round trip before going to Bobby's. Don't wonder about this just put it behind you. The two of you have bigger problems. Trust me." With that he vanished, just vanished.

"I don't know about you Dean, but I say we listen." With a nod he moved to slip into the drivers seat when something tugged at his wrist. He forgot about the cuffs.

"I'll slide through the passenger side." He didn't say anymore, Sam wouldn't want to talk about it either. They got in and drove, not talking until they had to switch cars. They found a small neon and slipped out together once more. Sam opened the driver door and leaned down to hot wire it. He pulled on his left hand and Dean crouched as well. It was awkward work but they figured it out. Soon they were back on there way to Bobby's.

"Should we really be going to Bobby's?" Sam looked over at him.

"Why not?"

"Well that's exactly where he told us to go. Should we maybe get a phone, call first?"

"No, we can't risk it. We'll just go to Bobby's and be careful."

"Then we can borrow something to get these off." Sam raised his left hand which brought Dean's right with it. Dean shook his head while thinking of what Bobby will say.

"Once again, we are so screwed.

...

**I think that was my fastest update ever**

**I know this chapter was slightly slow, but I needed Gabriel in it**

**Please review!**


	6. Problems and Tricks

**Disclaimer: I don't own Supernatural**

**Well now I have a pretty good idea where I'm going with this but I am always open to suggestions, please enjoy!**

...

"How the hell did you manage this?" Bobby was looking at their hands cuffed together in the kitchen. The two of them were sitting side by side each with a beer.

"We were in a hurry, it was either go back for the key and be shot or leave and live." Dean took a sip. "Now can you get these off of us please?"

"Why would I do that, you're so cute together." Bobby chuckled at their expressions.

"Bobby, drop it." Sam was agitated again, he couldn't help it anymore.

"Alright, alright." He sighed and pulled a lock pick out of his pocket and went to work. It wasn't five minutes and they were out.

"Thanks." They both spoke at the same time.

"So what the hell happened?" Bobby sat down across from them and listened intently as they recapped from the time Dean left here.

"So we still have no clue who or what the guy was, but he saved us." Sam finished off the story the same time he finished his beer. Dean brow was furrowed in thought. "What?" Sam asked kicking him in the shin.

"Well I think we should leave it as a mystery. Who knows what he'll do if we find him. He might just return us to the cops, or kill us himself."

"We also have two other problems." Bobby butted into the conversation to stop the oncoming argument.

"What's that?"

"Well Lilith for one, and the angels wont be too happy either. We're fighting a war with both sides now." His comment was met with silence.

...

Bobby's house could be defined as scary at night. All the weapons hanging around and the strange pictures. Still it didn't bother Sam; not when he had bigger problems. He slipped out the front door and moved to one of the cars Bobby kept for driving around to hunts. He quickly pulled out and headed down the road. Inside it was killing him to go on this hunt without Dean, but he had too. After an hour he ended up at a small rundown house. Pulling out Ruby's knife he moved to the back, the door was open and he moved in checking every room until he came to the kitchen. He could hear voices on the inside.

"We should leave town, we've been here too long." It was a female voice, she didn't sound too old.

"Oh come on, we can at least stay until morning. I like it here." A male voice sounding around the same age responded. He sounded close to the door so Sam made his move. Opening the door he knocked the man to the floor. He was in his early twenties. With a quick slit to the neck he burnt out. Jumping up he pinned the girl to the wall.

"Sam Winchester, what a pleasure to meet you." She sneered as he pushed the knife a little closer to her neck.

"Well it's never a pleasure to meet a demon." His heart was thrumming hard now.

"Are you sure about that? I'm pretty sure you didn't just come here to kill us Sammy." She laughed and smiled.

"That doesn't matter, you will still be dead in the end." He made a nick on her neck with the knife. Slowly he pressed his lips against it. It wasn't the taste that made him crave it, it was the feeling. The power began to fill him again until she was almost drained.

"Feel better boy?" Her breathing was uneven and when he let go she fell to the floor. Closing his eyes Sam concentrated, the life blinked out of her and he sighed opening his eyes once more.

"Much, thank you for asking." He walked out the back door and started back to his car, not agitated anymore. On the drive back he began to worry that they might have noticed his absence.

"They don't know your gone." Sam slammed on the breaks grabbing for the knife until he noticed it was gone. That was when he noticed who it was. The Trickster.

"What are you doing here." Sam moved his one hand to the door handle. The Trickster was inspecting Ruby's knife.

"I'm here to warn you." Finally he made eye contact with Sam. "If you don't stop your private business it will lead you right back to Lilith. You need to stop it for everyone's sake Sam." Sam glared at him his pulse quickening.

"Don't pretend to know anything about my life you monster."

"Now who's the real monster here," he handed Sam back the knife. "Remember what I said." With that he vanished. Sam sighed pulling back off the side of the road thinking even harder. When he pulled back into Bobby's he stayed outside watching the sunrise. Things had to get better, had to start making sense soon. They just had too.

...

**I know, I made Sam a blood junkie. Don't worry he's still Sam**

**I hope you enjoyed, please review!**


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